Synthesis, in vitro urease inhibitory potential and molecular docking study of Benzimidazole analogues

Zaman, Khalid; Rahim, Fazal; Taha, Muhammad; Ullah, Hayat; Wadood, Abdul; Nawaz, Mohsan; Khan, Fahad; Wahab, Zainul; Shah, Syed Adnan Ali; Rehman, Ashfaq Ur; Kawde, Abdel‐Nasser; Gollapalli, Mohammed

doi:10.1016/j.bioorg.2019.103024

Cited by 49 publications

(33 citation statements)

References 36 publications

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“…Necessary reagents for the synthesis of the targeted heterocyclic compounds (1)(2)(3)(4) NMR and IR were used for characterize the structures of the compounds obtained. In Erciyes University Central Research Laboratory, both 1 H NMR and 13 C NMR spectra were taken with Bruker Ultra Shield 400 MHz NMR Spectroscopy using CDCl3 or DMSO-d6 solvents.…”

Section: Reagentsmentioning

confidence: 99%

“…Compounds containing benzimidazole nucleus demonstrate a wide variety of biological activity properties such as anticancer, antitubercular antimicrobial, antifungal, antioxidant, antidiabetic and etc [1][2][3][4][5][6][7][8][9][10][11][12][13]. On the other hand, heterocyclic benzimidazole derivatives have different application area and can be used as catalysts [14][15][16] and sensors [17,18].…”

Section: Introductionmentioning

confidence: 99%

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Suzuki-Miyaura Çapraz Eşleşme Reaksiyonunda Katalizör Olarak Heterosiklik Bileşiklerin Uygulanması

Akkoç

2019

Cumhuriyet Science Journal

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Four different benzimidazolium salts (1-4) were prepared in three steps at 80 o C and their structures were elucidated using spectroscopic methods. The compounds (1-4) obtained were tested in in situ medium as catalyst in the carbon-carbon (C-C) bond formation reactions of two different boronic acid derivatives with various aryl halides in the presence of palladium acetate (PdOAc)2 and sodium tertiarybutoxide (NaOBu t) as a base. With this reaction, four coupling products (5-8) were synthesized in different yields ranging from 11 to 93%. Compound 2 from the carbene precursors tested in the Suzuki-Miyaura cross-coupling reaction was found to be a more effective catalyst candidate than others.

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Section: Reagentsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Suzuki-Miyaura Çapraz Eşleşme Reaksiyonunda Katalizör Olarak Heterosiklik Bileşiklerin Uygulanması

Akkoç

2019

Cumhuriyet Science Journal

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“…The heterocyclic benzimidazole nucleus is widespread in nature and present in several bioactive compounds. Benzimidazole is also a privileged ring in medicinal chemistry and this pharmacophore is included as a key part in antimicrobial, anticancer, acetylcholinesterase, antiprotozoal, anti-inflammatory, analgesic, antihistaminic, antiallergic, enzyme inhibitory, antimalarial, antitubercular, and antiviral agents [ 1 , 2 , 3 , 4 , 5 , 6 , 7 ]. Several benzimidazole-based compounds have been also reported to possess antioxidant activity [ 1 , 8 , 9 , 10 , 11 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

In-Vitro Evaluation of Antioxidant, Antiproliferative and Photo-Protective Activities of Benzimidazolehydrazone Derivatives

et al. 2020

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In the search of multifunctional compounds we designed benzimidazole derivatives endowed with phenolic hydroxy groups and a hydrazone moiety as potential radical-scavenger and the antioxidant agents. The target molecules have been prepared by a simple synthetic procedure and tested for their antioxidant activity by DPPH, FRAP, and ORAC test, for photoprotective activity against UV rays and for antiproliferative activity against Colo-38 melanoma cells. Furthermore, two different dermocosmetic formulations were prepared with the compounds endowed with the best antioxidant and photoprotective profile and their release from formulation evaluated using Franz Cells system. High antioxidant activity is related to the presence of at least two hydroxy groups on arylidene moiety of benzimidazoles. Structure activity analysis revealed that the position of hydroxy groups is crucial for antioxidant activity as well as the presence of a 2-hydroxy-4-(diethylamino)arylidene group. The same correlation pattern was found to be related to photoprotective activity resulting in an UVA Protection Factor better than the commercial solar filter PBSA and antiproliferative activity against melanoma cells without producing cytotoxicity on normal keratinocytes. The release analysis indicated that high antioxidant activities are achieved with limited release at concentration compatible with the use as UV sunscreen filter.

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“…Recently, we reported benzimidazole-based oxadiazole as an anti-alpha-glycosidase [ 20 ], benzimidazole-bearing bis-Schiff base as alpha glucosidase inhibitor [ 21 , 22 , 23 ], and 2-mercaptabenzimidazole as alpha amylase inhibitor [ 24 ]. Benzimidazole is a potent urease inhibitor [ 25 ]. Here, we report two new series of benzimidazole thiosemicarbazides and benzimidazole Schiff bases as novel Alzheimer inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Benzimidazole–Based Analogs as Anti Alzheimer’s Disease Compounds and Their Molecular Docking Studies

et al. 2020

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We synthesized 10 analogs of benzimidazole-based thiosemicarbazide 1 (a–j) and 13 benzimidazole-based Schiff bases 2 (a–m), and characterized by various spectroscopic techniques and evaluated in vitro for acetylcholinesterase (AchE) and butyrylcholinesterase (BchE) inhibition activities. All the synthesized analogs showed varying degrees of acetylcholinesterase and butyrylcholinesterase inhibitory potentials in comparison to the standard drug (IC50 = 0.016 and 4.5 µM. Amongst these analogs 1 (a–j), compounds 1b, 1c, and 1g having IC50 values 1.30, 0.60, and 2.40 µM, respectively, showed good acetylcholinesterase inhibition when compared with the standard. These compounds also showed moderate butyrylcholinesterase inhibition having IC50 values of 2.40, 1.50, and 2.40 µM, respectively. The rest of the compounds of this series also showed moderate to weak inhibition. While amongst the second series of analogs 2 (a–m), compounds 2c, 2e, and 2h having IC50 values of 1.50, 0.60, and 0.90 µM, respectively, showed moderate acetylcholinesterase inhibition when compared to donepezil. Structure Aactivity Relation of both synthesized series has been carried out. The binding interactions between the synthesized analogs and the enzymes were identified through molecular docking simulations.

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Synthesis, in vitro urease inhibitory potential and molecular docking study of Benzimidazole analogues

Cited by 49 publications

References 36 publications

Suzuki-Miyaura Çapraz Eşleşme Reaksiyonunda Katalizör Olarak Heterosiklik Bileşiklerin Uygulanması

Suzuki-Miyaura Çapraz Eşleşme Reaksiyonunda Katalizör Olarak Heterosiklik Bileşiklerin Uygulanması

In-Vitro Evaluation of Antioxidant, Antiproliferative and Photo-Protective Activities of Benzimidazolehydrazone Derivatives

Synthesis of Benzimidazole–Based Analogs as Anti Alzheimer’s Disease Compounds and Their Molecular Docking Studies

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